An avid listener of the Boston sports radio station for years, the 28-year-old software sales executive is turned off by the current roster of on-air personalities, whom he considers either overbearing or underwhelming, and disappointed by recent news that the station will no longer broadcast Boston Celtics games on 93.7 FM.

Once a Boston radio powerhouse that had the local sports market to itself, WEEI already has lost many listeners like Mavrikos to 98.5 The Sports Hub, a CBS-owned rival that was launched in 2009. Though the station takes in much more money than its new competitor, revenues at WEEI are down nearly 20 percent since The Sports Hub began broadcasting, according to industry figures, and it remains saddled with an expensive contract to broadcast the Boston Red Sox

Turnover has been high — it fired some of its biggest names, while others have quit. Longtime program director Jason Wolfe, who led the station during its most successful years, got his pink slip two weeks ago.

“They had so many opportunities to become complacent over there. They had the Sox on that amazing run, the economy was hot,” said Scott Fybush, who edits the trade publication NorthEast Radio Watch.

But while WEEI’s problems are serious, Fybush said, they are not fatal. “Look, ’EEI may be hurting. It is certainly far from dead.”

The company that owns WEEI, Entercom Communications, says it will continue with the current format and programming and argues WEEI’s brand remains strong. Officials point to the station’s sports-news website, WEEI.com, which they said drew 1.4 million unique visitors last month.

“We’re very pleased with the macro perspective of where WEEI is today, when you look at our big-picture plan,” said chief executive David Field. “We want to make ’EEI into more than just a radio station. We want it to be a multifaceted sports platform across New England.”

But it is the radio station that anchors the business, and here Entercom is feeling the repercussions of several major decisions that analysts said have proved costly: failing to take seriously the arrival of the Sports Hub; reluctance to switch from AM to the crisper sound of FM favored by younger listeners; unwillingness to update long-successful talk formats grown stale; and overpaying for the Red Sox broadcast rights in a 10-year, $200 million deal.

While The Sports Hub broadcasts the New England Patriots and Boston Bruins games, the loss of the Celtics leaves WEEI with just the Red Sox — a powerful draw, but an expensive one, too. The annual payment to the Red Sox eats up much of WEEI’s revenues. Moreover, the company faces big personnel decisions. Contracts with longtime morning hosts John Dennis and Gerry Callahan expire next year, and critics feel the duo exemplifies the station’s problems: They are highly paid — reportedly in the $1 million a year neighborhood — and can be polarizing; their talk often veers off into politics, and some former listeners complain they sound shrill or confrontational.

“I used to listen to ’EEI a lot, but they turned me off with their arrogance and their we’re-smarter-than-everybody attitude,” said Jonas Osborne, a friend of Mavrikos who has switched to The Sports Hub. “Dennis and Callahan are the worst. The way they treat callers — somebody will call in and I’ll think they bring up a good point, and [Dennis and Callahan] will just blow him off and say he doesn’t know what he’s talking about.”

Osborne prefers the more lighthearted approach of Sports Hub hosts Fred Toucher and Rich Shertenlieb, former rock DJs who make frequent detours from sports into music and pop culture.

Dennis defended the style of his show, saying the hosts’ occasionally abrasive tone prompts listeners to be more engaged.

“If you don’t ruffle the feathers of your listeners, then you’re not doing your job,” he said. “And the end result of that is you have some people upset with you. But the last thing I want to do is say, ‘Oh yes, I agree with you. That’s a very good point.’ That’s not good radio. Good radio is stuff that prompts people to respond and react.”

Field said he remains a fan of “The Dennis & Callahan Morning Show” and envisions it continuing for years.

More broadly, he downplayed the competition between WEEI and The Sports Hub, saying a sports-crazed market like Boston can easily sustain two stations.

“We have two very successful sports stations with huge audiences that are both doing great work and are very effective for their advertisers,” Field said. “That’s really the big picture, when you frame it from a business perspective. We’re going to continue to fight for the crown, but we’re both thriving.”

Yet the Red Sox deal has become an unexpected financial burden on WEEI, said Fybush. Entercom’s agreement in 2006 to pay an average of $20 million per year made the Red Sox’ radio rights the most expensive in Major League Baseball, by far — about what two New York City radio stations combined pay to broadcast the Yankees and Mets.

Fybush said WEEI was pressed at the time to keep the Red Sox from signing with rival Greater Media, which reportedly was planning to create an all-sports FM competitor.

“They really wanted to do whatever they could to counter that,” Fybush said. “But now, I think everybody pretty much agrees they overpaid, and they’re paying the price. Nobody would do a deal like that today.”

Still, business remained good for WEEI in the immediate aftermath of re-upping with the Red Sox. The team won its second World Series in four seasons in 2007, helping WEEI attract advertisers and rake in an estimated $44.2 million in revenue, according to BIA/Kelsey, a Virginia firm that tracks media industry finances. By 2012, however, annual revenue was down to $35.5 million.

While WEEI’s revenue decline mirrors trends across the radio industry, Entercom reports in financial filings that its stations in the Boston area, which include WAAF and WRKO, have experienced declines compared to stations it owns in other markets.

It also disclosed that it reduced the declared value of those Boston broadcast licenses by $22.3 million because of declining market share and other factors. The company does not disclose license values or other financial information for individual stations.

Field said the Red Sox contract is manageable for a large company like Entercom and asserted the Sox are “clearly the number one sports franchise in the United States, and you couldn’t choose a better partner to have as your cornerstone.”

When CBS launched The Sports Hub in 2009, WEEI looked as strong as ever in early Arbitron ratings books. On air, the station’s hosts mocked and shrugged off the challenger.

By its first anniversary, however, The Sports Hub had surged into first place during the morning- and afternoon-drive time slots among 25- to 54-year-old men.

The Sports Hub has often topped WEEI in key time periods ever since.

In February, Entercom fired host Glenn Ordway, a fixture at WEEI for 27 years. Several other longtime staffers left soon after. The biggest shakeup came with the firing of Wolfe, who had held various leadership positions at the station since it adopted an all-sports format in 1991.

“I don’t know all the ins and outs of what’s going on with ’EEI,” said Mavrikos, the longtime listener. “But I’m starting to lean more toward 98.5. I just find the other guys are better.”

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